| 1 | Sat 10 Aug 2019 | 1-0 v Shrewsbury TownMilton Keynes Dons 1-0 Shrewsbury Town | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 2-2 v AFC WimbledonAFC Wimbledon 2-2 Milton Keynes Dons | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 2-3 v Wycombe WanderersWycombe Wanderers 3-2 Milton Keynes Dons | Sky Bet League One |
| 4 | Tue 20 Aug 2019 | 2-1 v Lincoln CityMilton Keynes Dons 2-1 Lincoln City | Sky Bet League One |
| 5 | Sat 24 Aug 2019 | 0-4 v Peterborough UnitedMilton Keynes Dons 0-4 Peterborough United | Sky Bet League One |
| 6 | Tue 27 Aug 2019 | 4-1 v Southend UnitedSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 7 | Sat 31 Aug 2019 | 1-2 v Accrington StanleyAccrington Stanley 2-1 Milton Keynes Dons | Sky Bet League One |
| 8 | Tue 3 Sep 2019 | 3-0 v StevenageStevenage 0-3 Milton Keynes Dons | Leasing.com Trophy Southern Group G |
| 9 | Sat 7 Sep 2019 | 2-1 v AFC WimbledonMilton Keynes Dons 2-1 AFC Wimbledon | Sky Bet League One |
| 10 | Tue 17 Sep 2019 | 0-1 v Ipswich TownMilton Keynes Dons 0-1 Ipswich Town | Sky Bet League One |
| 11 | Wed 25 Sep 2019 | 0-2 v LiverpoolMilton Keynes Dons 0-2 Liverpool | Carabao Cup Third Round |
| 12 | Sat 28 Sep 2019 | 1-2 v SunderlandSunderland 2-1 Milton Keynes Dons | Sky Bet League One |
| 13 | Sat 5 Oct 2019 | 0-3 v Burton AlbionMilton Keynes Dons 0-3 Burton Albion | Sky Bet League One |
| 14 | Sat 12 Oct 2019 | 0-1 v Bristol RoversBristol Rovers 1-0 Milton Keynes Dons | Sky Bet League One |
| 15 | Tue 22 Oct 2019 | 0-2 v RochdaleRochdale 2-0 Milton Keynes Dons | Sky Bet League One |
| 16 | Sat 26 Oct 2019 | 0-1 v Fleetwood TownFleetwood Town 1-0 Milton Keynes Dons | Sky Bet League One |
| 17 | Sat 9 Nov 2019 | 0-1 v Port ValeMilton Keynes Dons 0-1 Port Vale | Emirates FA Cup First Round |
| 18 | Sat 16 Nov 2019 | 0-1 v Bolton WanderersBolton Wanderers 1-0 Milton Keynes Dons | Sky Bet League One |
| 19 | Sat 23 Nov 2019 | 2-3 v Rotherham UnitedMilton Keynes Dons 2-3 Rotherham United | Sky Bet League One |
| 20 | Tue 3 Dec 2019 | 2-0 v Coventry CityMilton Keynes Dons 2-0 Coventry City | Leasing.com Trophy Second Round |
| 21 | Sat 14 Dec 2019 | 1-0 v Oxford UnitedMilton Keynes Dons 1-0 Oxford United | Sky Bet League One |
| 22 | Sat 21 Dec 2019 | 1-3 v GillinghamGillingham 3-1 Milton Keynes Dons | Sky Bet League One |
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